IVAS 2022 banner
IVES 9 IVES Conference Series 9 IVAS 9 IVAS 2022 9 Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Hemisynthesis, NMR Characterization and UHPLC-Q-Orbitrap /MS² identification of (+)-Catechin oxidation products in red wines and grape seed extracts

Abstract

(+)-Catechin—laccase oxidation dimeric standards were hemi-synthesized using laccase from Trametes versicolor in a water-ethanol solution at pH 3.6. Eight fractions corresponding to eight potential oxidation dimeric products were detected. The fractions profiles were compared with profiles obtained with two other oxidoreductases: polyphenoloxidase extracted from grapes and laccase from Botrytis cinerea. The profiles were very similar, although some minor differences suggested possible dissimilarities in the reactivity of these enzymes. Five fractions were then isolated and analyzed by 1D and 2D NMR spectroscopy. The addition of traces of cadmium nitrate in the samples solubilized in acetone-d6 led to fully resolved NMR signals of phenolic protons, allowing the unambiguous structural determination of six reaction products, one of the fractions containing two enantiomers. These products were then analyzed in grape seed extracts and red wines (UHPLC-Q-Orbitrap MS). The different dimers had different fragmentation patterns according to their interflavan linkage position. Oxidation dimeric compounds had a specific fragment ion at m/z 393, missing for B-Type dimers fragmentations. A fragment ion at m/z 291 occurred and was specific for oxidation dimeric compounds with a C-O-C linkage. Higher level oxidation products had abundant specific fragments: m/z 425, 397 and 245. These fragmentations were useful to identify them in complex samples such as grape seed extracts and wines. Three grape varieties and three ripening stages were selected and the corresponding seed extracts were obtained. The analyses revealed an increasing trend for the oxidation markers during grape ripening. The analysis of Syrah wines (2018, 2014, 2010) showed a decreasing trend of these molecules during wine ageing which might be due to further oxidation.

DOI:

Publication date: June 23, 2022

Issue: IVAS 2022

Type: Article

Authors

Saucier Cedric1, Deshaies Stacy1, Le Guernevé Christine1,2, Sommerer Nicolas1,2, Garcia Lucas Suc François1, Mouls Laetitia1

1SPO, Université de Montpellier, INRAE, Institut Agro, UMR SPO, Faculté de Pharmacie, 15 avenue Charles Flahault, 34000 Montpellier, France
2INRAE, PROBE Research Infrastructure, PFP Polyphenol Facility, 34060 Montpellier, France

Contact the author

Keywords

wine, grape, polyphenol,oxidation, catechin

Tags

IVAS 2022 | IVES Conference Series

Citation

Related articles…

Foliar application of urea improved the nitrogen composition of Chenin grapes

The nitrogen composition of the grapes directly affects the developments of alcoholic fermentation and influences the final aromatic composition of the wines. The aim of this study was to determine the effect and efficiency of foliar applications of urea on the nitrogen composition of grapes. This study was carried out during 2023 vintage and in the Chenin vineyard located in Estacion Experimental Mendoza (Argentina). Three urea concentrations 3, 6 and 9 Kg N/ha (C1, C2, and C3, respectively) and control (T) were applied in this vineyard at veraison.

Read More

Terroir and vine water relation effects on grape ripening and wine quality of Syrah/R99

A Syrah/R99 vineyard in the Stellenbosch area was used. The vineyard is vertically trained and spaced 2.75 x 1.5 m in north-south orientated rows on terroir with Glenrosa soil and west-facing slope. Irrigation (to 100% field water capacity) treatments were applied at different development stages [all stages (including berry set stage); pea size; véraison; post-véraison]. Combined effects of water status and ripeness level were investigated. Preliminary results are presented.

Read More

The effects of cane girdling on berry texture properties and the concentration of some aroma compounds in three table grape cultivars

The marketability of the table grapes is highly influenced by the consumer demand; therefore the market value of the table grapes is mainly characterized by its berry size, colour, taste and texture. Girdling could cause accumulation of several components in plants above the ringing of the phloem including clusters and resulting improved maturity. The aim of the experiments was to examine the effect of girdling on berry texture characteristics and aroma concentration.

Read More

Evaluation of the hydroxyethyl radical formation kinetic and Strecker aldehydes distribution for assessing the oxidative susceptibility of Chardonnay wines

Over the last decade, much attention has been paid on the oxidative susceptibility of white wines, given its key role in determining their ageing potential.

Read More

Exploring high throughput secondary trait phenomics to improve grapevine breeding

Modern grapevine breeding programs have overcome many challenges using genomic selection, which has allowed breeders to make targeted selections at earlier stages in the breeding process. However, the cost of genetic testing may present a burden for some programs, and markers often struggle to accurately predict quantitative traits. Recent advances in high throughput, high-dimensional data have provoked investigation into the use of high-dimensional phenomics as a low-cost addition to the grape breeder’s toolkit that may offer advantages in predicting quantitative traits. High-dimensional secondary trait (HDST) data has been employed in annual crops for prediction of agriculturally important traits such as yield.

Read More